Madonna Singles Ranked, 11-20

Every few days or weeks, I pick a music artist or band, compile a chronological playlist of all of their singles (based on Wikipedia, Discogs and a few other sources) and then try to arrange that playlist in such a way that I like each song more than the previous song. Rearranging the songs is a never ending process so once I’m at a point where I think I’m pretty close to how I feel, I share the results with you 10 or so songs at a time. I’ve come to define “singles” in a pretty broad way so that it includes any song that was used to promote an album (via video or single) or any song that charted in a significant way. Generally speaking, I don’t include remixes or live versions of songs that were previously released as singles.

20. Physical Attraction\

From 1983’s Madonna, Brazil-Only A-Side

This song serves as a good example of how my brain works in regards to 80’s Madonna. I don’t recall ever hearing this song in the 80’s. When I first heard it later (probably in the late 90’s), I didn’t know it was Madonna and thought it was a great 80’s new wave hit that I’d somehow missed. This was before apps like Soundhound (or apps at all) so I wasn’t able to easily figure out who the song was performed by (short of singing it for friends). Heck, this was before Google. Anyhow, by the time I found out it was Madonna, I was all like “Oh, that’s cool.” Thus, I have no immediate inner-15-year-old reaction to this song and can just enjoy it for what it is. I’m almost 50 and part of my subconscious is directed by pissy high school sophomore me. Let’s contrast this reaction with…

19. Borderline

From 1983’s Madonna, Fifth Single

WXCI (Western Connecticut State University’s radio station) was the best radio station in Fairfield County as far as I was concerned. They played all the music that wasn’t getting any airplay on top 40 or rock radio. The first time I turned to that station, I was put off by the fact that I didn’t know any of the music. However, since a bunch of my friends were listening to it, I slogged through and pretty quickly decided it was the only station for me. Back in 82-83, Madonna was on regular rotation on that station because her songs fit in perfectly next to Depeche Mode and Yaz. Borderline was, in my memory, the song that got the most airplay. The synth-heavy sound of this track was still breaking in at this point – the Human League had just had the first all-synthesizer #1 hit with “Don’t You Want Me” the year before. It was always a big deal to me when a song from WXCI became a hit but I was already becoming a little suspicious of Madonna’s success by the time it was released. Where I was amped by the success of “Lucky Star” and “Holiday,” (“yay, one of ours is making it!”) I was starting to think Madonna was a bit of a sell-out. I started turning off the radio (or turning to a rock station) when this song would come on. The thing is, this was not in reaction to the song itself but to the idea of the song’s success. I liked that there was some music that was “mine” because most of my other friends didn’t listen to it. Tribal markers are a big deal, especially (but not limited to) when you’re a kid. All these years later, I can finally listen to the song again and hear it in its melancholy glory. After an initial cringe.

18. Drowned World (Substitute for Love)

From 1998’s Ray of Light, Third Single (not released in US)

The gorgeous opening track from Ray of Light was released as the third single from that album everywhere but the USA due to some record company calculus about release dates. In some ways, the song is a continuation of the story of “Bad Girl” – one night stands and fame and drink were all substitutes for love. Madonna (the character and possibly the human) has had a spiritual awakening and is looking for more authentic love (both in the form of spirituality and through motherhood, again assuming we’re talking about what Madonna was actually experiencing in 1998). “Frozen,” the first single, alerted the world that Madonna was approaching music differently. This track is the theme statement for the whole Ray of Light album but it works equally well as a stand alone single. Really gorgeous.

17. Justify My Love

From 1990’s The Immaculate Collection, First Single

I first heard this song thanks to Wayne’s World on SNL. The song only makes a minor cameo appearance but I’d apparently missed the controversial video entirely (I don’t think I had cable in the 1990) and since I was spending more time as a DJ at KTUH (which meant I had cassette recordings of my shows to listen to instead of radio) I sort of was unaware this song even existed. Plus, it was released to promote a greatest hits collection so it wasn’t getting the same kind of push as a standard Madonna album maybe? Anyhow, somebody had to point out to me that sections of the Wayne’s World video were parodies of the “Justify My Love” video. I heard bits and pieces of the song over the years but am not sure I heard the whole thing until around the time of Ray of Light or maybe even Music. I assumed it was a track I’d not heard from Bedtime Story or Erotica (which I thought were her first forays into trip-hop) and I’m sort of blown away that she was creating music in this form in 1990. She was an early adopter! I think this is maybe Madonna’s most successful spoken word single – I feel like she’s had mixed results with this style. The song was written by Lenny Kravitz and Ingrid Chavez and you can hear similarities between this tune an some of Kravitz’s solo work from the time.

16. Living for Love

From 2014’s Rebel Heart, First Single

“Living for Love” is a joyous, uplifting song about having your heart broken (and being able to move on strong). Musically, its a pastiche of 25 years of Madonna’s work – there’s a choir, a techno beat, the kind of guitar work she’s occasionally favored in this century, and little aural call backs to 80’s and 90’s Madonna. Its all mixed together in such a way that it doesn’t call attention to itself, but if you’re a fan of classic Madonna, this might be the modern track you begrudgingly like a little bit. 31 years after the release of her first album and she created another effortlessly catchy and exciting debut single.

15. Hollywood

From 2003’s American Life, Second Single

American Life is a bit of a transitional album for Madonna. Her previous two albums – Ray of Light and Music – were both full of music that was uplifting and very contemporary. She sounds restless on American Life. Her lyrics are more restless and cynical and she’s starting to feel uncomfortable with the restraints of this particular music style. “Hollywood,” I think, is the last great song from this period of her career (though not her last great song). Its really interesting to contrast it with the hope of the song “Ray of Light.” If that song is about rising to a higher, “Hollywood” is about rolling around in the grime and dirt – doing what you’ve got to do to succeed in a business that prefers youth and compliance. The relentlessness of the beat on this one (and the sense that Madonna can’t stop talking even though she’d like to) make this track very compelling to me, though I gather from poking around online that I’m in an extreme minority of people who are so compelled.

14. Like a Virgin

From 1984’s Like A Virgin, First Single

Thesis have been written about this song. Its the subject of a Tarentino monologue. The best Pop-Up-Video was designed around it. I have nothing worthwhile to add to the body of work on this song. I used to hate it. Now I love it. That keyboard bass… her vocal… yeah, this is one of the ultimate tunes of the 80’s.

13. Die Another Day

From the soundtrack to the 2002 film Die Another Day, First Single

If we learned nothing else from the Jason Bourne movies, its that a throbbing electronic beat works great as a spy movie theme. Madonna was in the middle of her electronica phase in 2002 so it should have been no surprise when her theme for the contemporary James Bond picture was an anxious techno number instead of a “Spy Who Loved Me” torch song (side note – that’s my karaoke song when I feel like I can get away with it). The song is tense and dramatic. The string stabs link it to other Bond themes but it really doesn’t sound like a traditional 007 theme at all. Good. Bond needed to be shaken up back then. Still, this is only her second best song from a spy movie.

12. Human Nature

From 1994’s Bedtime Stories, Fourth Single

There was a public backlash after Madonna’s Erotica album and Sex book. It was a touch of media over-saturation combined with a puritanical push-back against a woman owning her own sexuality and suggesting that all women (all people, too, by the way) can be comfortable owning their sexuality. “Human Nature” is her response to the whole push back. She took a pile of hatred from her critics and turned it into one of her best songs. I love singing along with the backing vocals especially. Express yourself don’t repress yourself indeed.

11. Beautiful Stranger

From the Soundtrack to the 1999 film Austin Powers: The Spy Who Shagged Me, First Single

This is Madonna’s best song from a spy movie. We manage to tie together two Mike Myers characters and two spy movies in one chunk of songs. I swear this is a coincidence and not by design. When I first heard this song, I assumed (for reasons that I can’t recall) that this was going to be the final Madonna single – a glorious late 20th century melange of 60’s swinging psychedelia and contemporary techno. I love singing along with this song from start to finish, but especially the “I looked into your eyes…” sections. The best part of this song for me is that Madonna seems to be genuinely having fun both singing it and performing the video. I love it when she just cuts loose.